Sophomore year in college I rented an inexpensive room in a house not far from campus from Gina, a 43-year-old divorced woman with big tits and a cute face.

We got on well, though at times I suspected that she would have liked more than a landlady-tenant relationship.

One day when I came home from class, on the way to my room I passed Gina’s bedroom and heard what sounded like moans. I peeked in to make sure she was okay, then froze. She was on her bed with a large black dildo lodged in her hairy pussy. She was as surprised as I was, but a lot less embarrassed.

I mumbled an apology and started to leave, but Gina called after me to come back. I went in hesitantly and sat on the edge of the bed, then noticed that she had a porn video playing on the TV with the volume way down. On-screen a black guy was fucking the hell out of a fat white chick. With my cock raging, I kept looking back and forth between the TV and Gina’s cunt, which was split by the dildo.

She smiled at me and reached for my zipper and pulled it down. She took out my cock and declared, “My, what a lovely thing you have.” She moved down on the bed so she could take it in her mouth and in a few minutes was swallowing my load.

When I recovered from my surprise, I asked Gina if she watched porn often. She said she did. She added that there was an adult theater in the next town she’d always wanted to go to but had always been too nervous. I suggested she go with me, like she obviously wanted, and we made a date for the next night.

Then she sucked me hard again, and this time I climbed up between her thick thighs and drove my cock in her cunt. She was warm and soft, and I fucked her hard, and she didn’t complain. And she let me shoot in her, unlike most of the girls I’d been with.

When I got home the next night Gina was waiting in a knee-length skirt and a tight blouse that showed off her big tits. She pulled out a box in which there was a red wig, a stuffed bra, stockings, a skirt and a pair of high heels. I asked what the stuff was for, and she said she wanted me to wear it!

I said, “No fucking way!” But she begged, and even said she’d give me my next month’s room and board free. That was tempting! Besides, I was kind of curious about crossdressing. So I figured what the hell?

Gina helped me shave my legs and get into the clothing. The black lace-top stockings felt incredible on my now-smooth legs. Then she put some makeup on me, and the wig. When she was done, I looked in the mirror and had to admit I looked pretty damn sexy. I started feeling kind of excited. A little nervous too, but I was determined to do it!

Gina told me her ex-husband used to dress up for her, and they’d gone to that theater a few times before he left her for “some broad.” So she’d been there before! I had to wonder why she’d lied about that.

When we got to the theater there was more action going on in the audience than on-screen. Even in the dark I made out a couple of guy-on-guy couplings, and also a couple of straight couples making out, surrounded by people watching. People checked us out as we entered, and Gina seemed to be checking them out as well.

Before I knew what was happening, she was leading me toward a black couple she seemed to recognize, and they seemed to know her too. They invited us to join them. They were Henry and Lenore, both in their 30s. They seemed nice. My nervousness subsided as we settled down to watch the show, with Gina and Lenore sitting next to each other between Henry and me.

After a few minutes I saw that the women were stroking each other’s legs. Soon they were playing with each other’s pussies. Then Henry began stroking Lenore’s other leg. As he did, he kept checking me out. I figured he had to know I was a guy, but he didn’t seem to mind!

Another guy came along and sat on my other side, and I soon felt his hand on my leg, stroking my stockings. I felt an electric thrill, and didn’t stop him when his hand moved higher. When he found a hard cock between my legs, he pulled it out and fondled it.

By now Gina and Lenore were locked in an embrace, with their hands buried in each other’s crotch. I looked down to see my cock being stroked by this stranger, and was weirded out by the sight of a male hand jerking me off. When I looked back at Gina, I saw that Henry had gotten up and moved between her spread thighs. He got down on his knees and began to explore her snatch with his mouth, tongue and fingers.

I had a sudden desire to do the same thing to Lenore, so I pulled away from the guy jerking me off and got in front of her. I was glad to find that she had no objection to me going down on her, like Henry was doing to Gina. This was the first black pussy I had ever eaten, and it was quite nice.

As I slurped away at Lenore’s crotch, I felt my skirt being pushed up, and looked around to see Henry behind me. Lenore quickly pulled my face back to her pussy, and as I went back to eating her, I felt something soft yet firm nudging at my ass. For a moment I went stiff, realizing what was about to happen. Then I heard Gina whisper in my ear, “It’s all okay, baby. Just relax and let him do it.”

So I did. I gasped and moaned into Lenore’s hot pussy as Henry gripped my hips and slowly pushed his cockhead inside me. When I felt it pop past my tight sphincter, I cried out with pleasure, but the sound was muffled by Lenore’s crotch. I heard other voices around me, and I realized a crowd had gathered to watch what was going on!

Henry’s cock kept moving deeper, and soon I had an entire black shaft in my ass. It was nearly splitting me in two, but it felt great! He began thrusting in me, even rolling his hips side to side in an effort to stretch me open further.

I became aware of someone else sliding under me to engulf my cock in his or her mouth. At first I thought it was Gina. Then I heard her talking to Henry, and he said to her, “He’s tight, Gina. Where’d you get this one?”

“He’s my tenant,” she said.

He said, “I like him.”

The joint sensation of Henry’s cock splitting my ass and the unknown mouth expertly sucking my cock became overwhelming, and I lost it, shooting in the unknown mouth just as Henry groaned and filled my ass with a load of hot come.

When Henry pulled out, my ass was throbbing and tingling pleasantly. I felt his come running out of me. But it wasn’t over. As Henry stepped away, I felt another cock probing my ass, and Lenore said, “Yeah, come on, guys, form a line.”

The new cock fucked me hard, and creamed my ass quickly. It was replaced by another, and another, until at least eight cocks had come in my now loose and welcoming ass. Other guys stood and watched, jerking off and shooting their come on me. I was a mess, but I’d had at least three climaxes of my own and had never felt so satisfied.

True to her word, Gina didn’t charge me rent for the next month — or for any month since, as I’m now hooked on dressing up and we go back to that theater often. We go other places too, such as Lenore and Henry’s house, where I always dress up and serve both Gina and Lenore as well as Henry and a few of his friends. It’s a lot of fun, and it pays the rent. Who could ask for more?